Kingsway Financial Services deepened its first-quarter loss on transition costs, a drop in trucking premiums and lower return on investments.

The insurer of truck drivers and high-risk car drivers said its loss widened to $58.3 million from a loss of $34.4 million in the same year-ago period.

The loss amounted to 99 cents per share, significantly higher than analyst estimates and compared to a year-earlier loss of 63 cents.

Quarterly revenues for the Toronto company dropped 34 per cent to $290.9 million from $443.1 million.

On May 7, a day before announcing its quarterly reports, Kingsway announced its intention to exit the Canadian cross-border trucking business by July 1 and warned it will further reduce staff.

It announced earlier in the year the elimination of 750 jobs or about 28 per cent of its total North American workforce to take place during the next 18 to 24 months.